JPH0322361B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula [] (In the formula, R1 represents a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, R2 represents a hydrogen atom or a hydroxyl group, and X represents a halogen atom or a lower alkyl group having 1 to 4 carbon atoms.
represents a lower alkyl group, n represents an integer from 0 to 2, and Z represents a hydrogen atom or a halogen atom. )
One or more compounds represented by
2,4-dichlorophenoxyacetic acid (hereinafter referred to as “2,4
-D"), 4-chloro-2-methylphenoxyacetic acid (hereinafter referred to as "MCP"), N-(dimethylamino)-succinamic acid (hereinafter referred to as "B-995" or methyl-2-chloro-9-hydroxy-fluorein) -(9)- This relates to a plant growth regulator containing a mixture with carboxylate (hereinafter referred to as "CF-125") as an active ingredient, and is particularly aimed at effectively dwarfing grasses such as grass and rice. As a plant growth inhibitor, the isonicotinic acid anilide compound represented by the above general formula [ ] is used as a plant growth inhibitor with a wide range of applications and high practical value.
For example, for rice, it can be widely used for raising seedlings in boxes, preventing the growth of seedlings, preventing aging, and preventing lodging of transplanted paddy fields. Although it is effective against all types of grass, it exhibits a particularly strong growth-inhibiting effect on plants belonging to the Poaceae family. Examples of effective plants include the rice mentioned above, as well as wheat, corn, and grass.
It also exhibits stable effects on broad-leaved plants. On the other hand, 2,4-D, MCP, B-995 and
CF-125 is a substance known as a plant growth regulator, and has already been used as a lawn growth inhibitor, rice lodging prevention agent, and
Although it is a useful drug as a flower dwarfing agent, it is not very effective when used alone, and in high doses, it can brown the leaves of useful plants, delay the growth of new leaves, and impair the aesthetic appearance. be. As a result of various studies to address these problems, the present inventors have found that the isonicotinic acid anilide compound represented by the above general formula [] and the above-mentioned known growth regulator are combined and treated with plants. It was discovered that this method does not cause any harm to useful plants and has an excellent growth regulating effect. That is, due to the additive effect, it exhibited a strong growth-inhibiting effect particularly on the grasses of the grass family, turf and rice, and in addition to extending the treatment period, unexpectedly, a synergistic effect was observed.
In other words, these compounds have a significantly greater ability to inhibit plant growth than when used alone, exhibiting a strong growth-inhibiting effect even on lawns with a complete saturation layer, and inhibiting rice lodging. As an inhibitor, no decrease in yield was observed at any time of treatment before heading. As described above, the present invention provides isonicotinic acid anilide compounds [] with 2,4-D, MCP, and B-995.
Or, it relates to plant growth inhibitors and lodging prevention agents that are formulated with plant growth regulators such as CF125, and is characterized by significantly improved performance as a plant growth regulator due to synergistic effects based on the combination of active ingredients. That is. Each of the above-mentioned plant growth regulators used in the mixture of the present invention is a known plant physiologically active substance as a plant growth regulator or herbicide. The development of synergistic effects of agents is novel. The plant growth regulating effect of the mixed use of known plant growth regulators other than those mentioned above and the isonicotinic acid anilide compound used in the present invention was also investigated, and most of the combinations were found to be useful. However, the combination with the above drugs was of high practical value. The compound of the present invention represented by the general formula [ ] is novel and can be produced by the method shown below. (1) General formula [] (In the formula, Y represents a halogen atom.) Isonicotinic acid halide represented by the general formula [] (In the formula, R1, R2, X, n and Z have the same meanings as above.) A compound represented by the general formula [] is produced by reacting with an aniline derivative represented by the formula []. In this case, the reaction will proceed more smoothly if a suitable deoxidizing agent is used. In addition, suitable solvents include pyridine, methanol, benzene, toluene, xylene, dichloromethane, chloroform,
Examples include tetrahydrofuran, dioxane, acetone, and dimethylformamide. As a deoxidizing agent, pyridine, triethylamine, caustic soda,
Examples include caustic potash, carbonated soda, and carbonated potash. The reaction may proceed at room temperature, but may be carried out with cooling or heating as the case may be. The temperature is preferably 0 to 60°C. Although the reaction time depends on the selection of conditions, it is completed in 1 to 8 hours. After the reaction is completed, the desired product can be obtained by separation and purification using conventional methods. (2) General formula [] (wherein R1, be able to. Examples of the reducing agent include lithium aluminum hydride and sodium borohydride. In actual practice, it can be easily produced by using a conventional method for each reducing agent. A manufacturing example will be given and explained below. Production example 1. N-methyl-isonicotinic acid-{4-chloro-
2-(α-Hydroxybenzyl)}anilide (compound number) Dissolve 15 g of 2-methylamino-5-chlorobenzhydrol in 30 ml of pyridine, cool the solution with ice while stirring, and dissolve isonicotinic acid chloride hydrochloride. Add 1.4g little by little. This requires approximately 30 minutes. After stirring for an additional 3 hours at room temperature, 200 ml of water was added to the reaction solution to precipitate crystals. When these crystals were collected and recrystallized from a methanol-acetone mixed solvent, N-methyl-isonicotinic acid-{4-chloro-2-(α-hydroxybenzyl)}anilide was obtained.
Get 1.7g. Melting point: 199-201℃ Elemental analysis value: C20H17CN2O2 (assuming molecular weight 351.81) C H N Calculated value (%) 68.08 4.86 7.94 Actual value (%) 67.96 4.98 7.79 In addition, by changing the solvent to pyridine, benzene, toluene, xylene, dichloromethane, The desired product was also obtained using chloroform, tetrahydrofuran, dioxane, acetone, and dimethylformamide. Production Example 2. Isonicotinic acid-{4-chloro-2-(α-hydroxybenzyl)}anilide (Compound No. 4) 1.9 g of isonicotinic acid-(4-chloro-2-benzoyl)anilide was dissolved in 20 ml of methanol. Add 0.2 g of sodium borohydride little by little to the solution while stirring. This will take approximately 30 minutes. Stirring was continued for an additional 2 hours at room temperature. After the reaction was completed, 200 ml of water was added to precipitate crystals. The crystals were collected by filtration and recrystallized from a dimethylformamide-methanol mixed solvent to obtain 1.8 g of isonicotinic acid-{4-chloro-2-(α-hydroxybenzyl)anilide. melting point
210-212℃. Elemental analysis value: C19H15CN2O2 (as molecular weight 338.79) C H N Calculated value (%) 67.36 4.46 8.27 Actual value (%) 67.18 4.56 8.29 In addition, the solvent was changed to methanol and pyridine, benzene, toluene, xylene, dichloromethane,
The desired product was obtained using chloroform, tetrahydrofuran, dioxane, acetone, and dimethylformamide. Production example 3. Isonicotinic acid (4-chloro-2-benzyl)
Anilide (Compound No. 1) Dissolve 1.3 g of 4-chloro-2-benzylaniline in 30 ml of pyridine, cool the solution with ice, and add 1.4 g of isonicotinyl chloride hydrochloride little by little while stirring. This will take approximately 30 minutes. Further at room temperature 3
Continue stirring for an hour to complete the reaction. When 200 ml of water was added to this reaction solution, crystals were precipitated. The crystals were collected and recrystallized from ethanol to obtain 1.6 g of isonicotinic acid-(4-chloro-2-benzyl)anilide. Melting point 178-179℃ Elemental analysis value: C19H15CN2O (assuming molecular weight 322.79) C H N Calculated value (%) 70.70 4.68 8.68 Actual value (%) 70.75 4.79 8.65 Next, it is expressed by the general formula [ ] obtained in this way. Table 1 shows representative examples of the compounds that can be used. The present invention is not limited only to these exemplified compounds. Note that the compound numbers are also referred to in the following Examples and Experimental Examples.

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[Table] The plant growth regulator of the present invention has the general formula []
A mixture of one or more of the compounds represented by the above and each of the above plant growth regulators is usually added per 10 ares.
It is appropriate to use it at a rate of 100 to 3000 g, preferably 150 to 2000 g, but it goes without saying that the amount can be adjusted as appropriate depending on the cultivation conditions, growth status, and type of the plant. For example, when processing foliage, 10
150 to 2000 g per are is appropriate, and when processing into seedling boxes (30 cm x 60 cm x 3 cm), use at a rate of 2 to 150 g per 10 are (20 boxes). In addition, for formulation, it can be mixed with various solid and liquid carriers used in the preparation of general agricultural chemicals to produce wettable powders, emulsions, powders, granules, etc. Furthermore, auxiliary agents such as dispersants, diluents, emulsifiers, penetrants, and binders may be added to the drug. Also,
Depending on the purpose of use, the above components can be used in combination with other herbicides, fungicides, insecticides, plant growth regulators, fertilizers, etc. The carrier referred to herein may be either solid or liquid. These examples include talc, clay, kaolin, diatomaceous earth, calcium carbonate, wood flour, starch,
Gum arabic, water, alcohol, kerosene, naphtha, xylol, xylene, cyclohexanone,
Methylnaphthalene, benzene, acetone, etc. are used as adjuvants used in drug formulations, such as nonionic agents (polyoxyethylene alkyl phenyl ether, ethylene oxide propylene), etc. (oxide copolymers, lignin sulfonates, sorbitan esters, etc.), anionic (soaps, sulfated oils, alkyl sulfate ester salts, petroleum sulfonates, dioctyl sulfosuccinate salts, alkylaryl sulfonates, etc.), Cationic (aliphatic amine salts, quaternary ammonium salts,
Examples include surfactants of the amphoteric type (alkylpyridinium salts, etc.) and amphoteric surfactants (alkylaminoethylglycine, alkyldimethylbetaine, polyglycol sulfate, alkylamine sulfonic acid, etc.). However, it goes without saying that the embodiments of the present invention are not necessarily limited to the above-mentioned dosage forms. In addition, when formulating, the mixing ratio is determined by the general formula []
5-45% of the compound represented by: 1-25% of the plant growth regulator: 0-15% of the surfactant: 30-94% of the carrier
is optimal. Note that depending on the dosage form, it is not necessary to add a surfactant. In addition, in the present invention, various insecticides, fungicides,
Herbicides, plant growth regulators, acaricides, nematicides,
By using it in combination with attractants, repellents, plant nutrients, fertilizers, etc., a wider range of effects can be expected. The chemical of the present invention may be used during, for example, the sowing period, the seedling period, or the growing period, and depending on the target plant, treatments such as spraying on the ground, water surface or soil, and immersion can be performed. Next, the effects of the present invention will be explained in detail by showing experimental examples. Experimental example 1. Fill a 1/5000 are plastic pot with sandy loam, sow Kentucky bluegrass, grow it using conventional methods for three years, cut the grass to a height of 0.5 cm, and then use the formulation shown in Example 1 below. A hydrating powder (isonicotine acid anilide compound, B-995 and CF-125 alone) was formulated in the same manner using the chemical method, and the concentration of the active ingredient in the composition was kept constant by increasing or decreasing the amount of clay. ) was diluted with water at a ratio of 100/10a to give the prescribed dose and treated. Thereafter, they were kept in a glass greenhouse until the day of the survey.
To investigate the effect, the height of the grass was measured 30 days after the chemical treatment, and at the same time, the grass was cut leaving 0.5 cm above ground, and its fresh weight was measured. The results are shown in Table 2.

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[Table] Experimental example 2. The green of a golf course where bentgrass is cultivated (grown for 5 years) was divided into sections of 2 m x 2 m, and the above-ground part was cut to a height of 0.5 cm, as shown in Example 2 below. Formulation method: Emulsion and none (Isonicotinic acid anilide compounds, B-995 and CF-125 alone were formulated in the same way, and the amount of xylene was increased or decreased to keep the concentration of the active ingredient in the tissue constant.) Dilute the sample with water to the specified amount and use a small feces container to make sure it adheres to the stems and leaves.
Sprayed at a rate of 10a. The effect was investigated on the 30th day after the chemical treatment by measuring the height of the grass and the fresh weight of the above-ground parts (plant height).
(cut to 0.5 cm) was measured. The results are shown in Table 3.

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[Table] Experimental example 3. Young rice seedlings (variety: Koshihikari) were mechanically transplanted in a paddy field using the conventional method (May 20, 1980), and the ears emerged at 42
1 day in advance, divide the area into 10 m ² sections, and prepare granules (isonicotinic acid anilide compound, 2,4-D, B-995 and MCP) using the formulation method shown in Example 3 below.
For single use, formulations were prepared in the same way, and the concentration of the active ingredient in the composition was kept constant by increasing or decreasing bentonite. )
A predetermined amount of the material was sown by hand. From now on, increase the water depth to 3
It was kept at ~5 cm. To investigate the effects, culm length was investigated on August 30th, and the degree of lodging was investigated on October 10th. The results are shown in Table 4.

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[Table] Examples of the present invention are shown below, but the compounds, carriers, and proportions used are not limited to these examples. Example 1. Compound No. 4 40 parts by weight CF-125 20 Sodium alkyl sulfate 5 Clay 35 These are thoroughly mixed until homogeneous and pulverized to obtain a wettable powder. When using this, dilute it with water to a predetermined concentration and spray. Example 2. Compound No. 1 20 parts by weight B-995 5 Polyoxyethylene phenyl ether 7 Calcium alkylbenzenesulfonate
3. xylene 40. cyclohexanone 25. Mix and dissolve these ingredients thoroughly until uniform to obtain an emulsion. When using this, dilute it with water to a predetermined concentration and spray. Example 3. Compound No. 5 10 Parts by weight 2,4-D 1.5 Bentonite 53 Diatomaceous earth 35.5 These are mixed until homogeneous, pulverized and granulated by a conventional method, and used as granules.

Claims (1)

[Claims] 1. General formula (In the formula, R1 represents a hydrogen atom or a lower alkyl group, R2 represents a hydrogen atom or a hydroxyl group, X represents a halogen atom or a lower alkyl group, n represents an integer from 0 to 2, and Z represents a hydrogen atom or a halogen ) and 2,4-dichlorophenoxyacetic acid, 4-chloro-2-methylphenoxyacetic acid, N
A plant growth regulator comprising -(dimethylamino)-succinamic acid or a mixture with methyl-2-chloro-9-hydroxy-fluorein-(9)-carboxylate as an active ingredient.